25-hydroxy-6-<3-(2-tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D3 | 244291-33-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 25-hydroxy-6-<3-(2-tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D3
• 英文别名: 25-hydroxy-6-<3-(2-tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃
• CAS: 244291-33-6
• 化学式: C₃₅H₅₈O₄
• 分子量: 542.843
• InChiKey: CWMPYZYYXLAPJC-USYAIHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  25-hydroxy-6-<3-(2-tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D3 在 咪唑 、 4-二甲氨基吡啶 、 氢氟酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.75h， 生成
  参考文献：
  名称：

  C-6 functionalized analogs of 25-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3: synthesis and binding analysis with vitamin D-binding protein and vitamin D receptor11Note: Stereochemistries of the 3- and 1-hydroxyl groups of vitamin D sterols are designated according to cholesterol nomenclature.

  摘要：

  In this article, we describe the development of a general synthetic strategy to functionalize the C-6 position of vitamin D-3 and its biologically important metabolites, i.e. 25-hydroxyvitamin D-3 (25-OH-D-3) and 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3]. We employed Mazur's cyclovitamin D method to synthesize vitamin D-3 analogs with several functionalities at the C-6 position. In addition, we synthesized 6-(3-hydroxypropyl) and 6-[(2-bromoacetoxy)propyl] derivatives of 25-OH-D-3 15 and 16, respectively, and 6-(3-hydroxypropyl) derivative of 1,25(OH)(2)D-3 17. Competitive binding assays of 15-17 with human serum vitamin D-binding protein showed that all these analogs specifically bound to this protein, although with significantly lower affinity than the 25-OH-D-3, the strongest natural binder. but with comparable affinity with 1,25(OH)(2)D-3, the hormone. On the other hand, 6-[3-hydroxypropyl], 1 alpha,25-dihydroxyvitamin D-3 17 did not show any specific binding for recombinant nuclear vitamin D receptor. These results indicated that the region containing the C-6 position of che parent seco-steroid [1,25(OH)(2)D-3] may be an important recognition marker towards vitamin D receptor binding. Information, delineated in this article, will be important for evaluating structure-activity relationship in synthetic analogs of vitamin D and its metabolites. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00009-4
• 作为产物：
  描述：

  在 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.58h， 生成 25-hydroxy-6-<3-(2-tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D3
  参考文献：
  名称：

  C-6 functionalized analogs of 25-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3: synthesis and binding analysis with vitamin D-binding protein and vitamin D receptor11Note: Stereochemistries of the 3- and 1-hydroxyl groups of vitamin D sterols are designated according to cholesterol nomenclature.

  摘要：

  In this article, we describe the development of a general synthetic strategy to functionalize the C-6 position of vitamin D-3 and its biologically important metabolites, i.e. 25-hydroxyvitamin D-3 (25-OH-D-3) and 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3]. We employed Mazur's cyclovitamin D method to synthesize vitamin D-3 analogs with several functionalities at the C-6 position. In addition, we synthesized 6-(3-hydroxypropyl) and 6-[(2-bromoacetoxy)propyl] derivatives of 25-OH-D-3 15 and 16, respectively, and 6-(3-hydroxypropyl) derivative of 1,25(OH)(2)D-3 17. Competitive binding assays of 15-17 with human serum vitamin D-binding protein showed that all these analogs specifically bound to this protein, although with significantly lower affinity than the 25-OH-D-3, the strongest natural binder. but with comparable affinity with 1,25(OH)(2)D-3, the hormone. On the other hand, 6-[3-hydroxypropyl], 1 alpha,25-dihydroxyvitamin D-3 17 did not show any specific binding for recombinant nuclear vitamin D receptor. These results indicated that the region containing the C-6 position of che parent seco-steroid [1,25(OH)(2)D-3] may be an important recognition marker towards vitamin D receptor binding. Information, delineated in this article, will be important for evaluating structure-activity relationship in synthetic analogs of vitamin D and its metabolites. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00009-4